SYNTHESIS OF ARA-3,7-DIDEAZAADENOSINE AND RELATED PYRROLO[3,2-C]PYRIDINE D-ARABINOFURANOSIDES

Autor(en): BOURGEOIS, W
SEELA, F
Stichwörter: 2',3'-DIDEOXYRIBONUCLEOSIDES; 2'-DEOXYRIBONUCLEOSIDES; Chemistry; Chemistry, Organic; D-RIBONUCLEOSIDES; LIQUID; PHASE-TRANSFER GLYCOSYLATION; RIBOFURANOSYL CHLORIDES
Erscheinungsdatum: 1991
Herausgeber: ROYAL SOC CHEMISTRY
Journal: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Ausgabe: 2
Startseite: 279
Seitenende: 283
Zusammenfassung: 
Pyrrolo[3,2-c]pyridine (3,7-dideazapurine) D-arabinonucleosides, including ara-3,7-dideazaadenosine 1, ara-3,7-dideazainosine 2, and ara-3,7-dideazanebularine 3 were synthesized from 1-(beta-D-arabinofuranosyl)-4,6-dichloro-1H-pyrrolo[3,2-c]pyridine 10. Compound 10 was obtained by glycosylation of the 4,6-dichloro-1H-pyrrolo[3,2-c]pyridine 5 anion (phase-transfer conditions) with the 2,3,5-tri-O-benzyl-D-arabinofuranosyl halides 6 or 7. The ratio of glycosylation products (beta:alpha) was 4:1 in the case of the bromide and 13:1 using the chloride. In contrast to ara-A, compound 1 is not deaminated by adenosine deaminase.
ISSN: 0300922X
DOI: 10.1039/p19910000279

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